The Secrets of Shoulder Season, the Most Underrated Time to Travel

We'll also answer the most commonly asked question: What is shoulder season, exactly?

It’s already Labor Day, and the daily grind looms large as the kids go back to school and beach towels and umbrellas are stashed for the season (sob). But like your summer tan, not all is undone. We’ve officially entered one of the travel world’s most coveted periods: the fall shoulder season. This small window still brings beautiful weather and long daylight hours—along with thinner crowds, cheaper hotels and flights, and an enchanting locals’ vibe. (Plus, reservations at those ‘it’ restaurants are so much easier to come by.)

So don’t store that luggage just yet. Here are some lessons we've learned to maximize travel during shoulder season.

SHOULDER SEASON DIFFERS BY DESTINATION

September and October constitutes fall shoulder season for many regions, though not all. Research your proposed destination beforehand to be sure you’re traveling at the right time (or cheat by scrolling through our gallery on 12 Ways to Enjoy an Endless Summer). In North America, some of our favorite fall getaways include Jackson Hole, Vancouver, B.C., and Nantucket. In the Mediterranean, consider Croatia, Montenegro, and the Greek Islands (hello, Santorini!).

CHECK FOR FLIGHTS FIRST

You may find an amazing hotel deal only to discover that most airlines have already stopped seasonal flights to your destination. A general rule is to fly by October 15 to reach spots with an extended summer; just keep in mind that some airlines may end their flight schedules on October 1. In addition, shoulder season typically means greater availability of mileage tickets, so this may be a good time to cash out your frequent flier miles.

BE SPONTANEOUS

While some places like New England, New York City, and Paris witness a high season in the fall, in general, you have your pick when it comes to beaches, national parks, and destinations that rely on family travel. Unlike, say, the Hamptons in summer or the Caribbean in winter, which require reservations months in advance, there tends to be plenty of hotel occupancy in places like Orlando, Martha's Vineyard, the Grand Canyon, and along Mexico's coastlines during shoulder season. This means there should be plenty of last-minute deals. Start looking at Google Flights, Fareness, or Concorde, a new flight deal website for impulsive travelers.

THINK PRE- AND POST-PEAK SEASON

In general, the fall shoulder season equals post-peak season in early fall. However, for places that thrive in winter, such as the Caribbean, you’ll want to visit pre-season, in late fall between Thanksgiving and mid-December, when hurricane season is over, the weather is glorious, and your dream resort is a fraction of what you’d pay for it January through March. But don’t worry if you can’t fit in another trip soon: There’s a spring shoulder season just around the corner, in April and May.